Homes for Sale near Staples High School

• 

  

  

  /40

  $2,474,000

  • 4 Beds
  • 5 Baths
  • 4,013 Sq Ft

  30 Cavalry Rd, Westport, CT 06880

  *THE HOME IS NOW 4600 Sq FT( Seller has finished an additional Sq ft that was previously unfinished)** Prepare to be wowed by this stunningly reimagined 4-bedroom, 3 full and 2 half bath masterpiece, set on over 2 acres of private, picturesque grounds with plenty of room for a pool. This home is fully equipped with the latest in smart home technology. The open-concept floor plan centers around a

  

  Hyleri Katzenberg

  Compass Connecticut, LLC

  (475) 275-9243

  30 Cavalry Rd, Westport, CT 06880
• 

  Explore Staples High School

• 

  

  

  /13

  $2,575,000

  • Land
  • 0.42 Acre
  • $6,130,952 per Acre

  48 Compo Mill Cove, Westport, CT 06880

  DIRECT WATERFRONT WITH 100' of PRIVATE BEACHFRONT AND RARE OPPORTUNITY TO BUILD A STUNNING HOME ON COMPO MILL COVE WITH A POOL. This is the lifestyle you have been dreaming of. A little slice of Paradise. Come breathe in the saltwater air and see all that this hidden jewel has to offer located on Compo Mill Cove, a gated private waterfront enclave of 19 homes. This property offers the rare

  

  Susan Lieberman

  The Riverside Realty Group

  (475) 256-6465

  48 Compo Mill Cove, Westport, CT 06880
• 

  

  

  /5

  $4,895,000 New Construction

  • 6 Beds
  • 9 Baths
  • 9,224 Sq Ft

  21 Warnock Dr, Westport, CT 06880

  Expected for completion Fall 2025, this striking architectural design meets refined luxury in a meticulously crafted 9,200+/- sq ft, 6-bedroom, 6 full, & 3 half bath new residence. Showcasing the collaborative excellence of AR Luxury Homes w/ interior design by Mary Beth Woods & architectural vision by Donald William Fairbanks, this exceptional property represents the pinnacle of modern

  

  Brett Lieberman

  The Riverside Realty Group

  (475) 255-6647

  21 Warnock Dr, Westport, CT 06880
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  /40

  $3,125,000

  • 6 Beds
  • 7 Baths
  • 9,454 Sq Ft

  25 Hermit Ln, Westport, CT 06880

  Discover the epitome of luxury in this beautifully furnished Colonial estate located in Westport's prestigious Red Coat neighborhood. Offering over 7,000 square feet of elegant living space plus an additional 2,400 square feet in the finished lower level, this 6-bedroom, 5.2-bath home is designed for both everyday comfort and grand entertaining. The gourmet kitchen is outfitted with Wolf

  Jolanta Rojek eXp Realty

  25 Hermit Ln, Westport, CT 06880
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  /40

  $3,895,000

  • 4 Beds
  • 3.5 Baths
  • 3,418 Sq Ft

  61 Clapboard Hill Rd, Westport, CT 06880

  Located in prestigious Greens Farms, this European-inspired Colonial captures the timeless romance of the countryside in a coveted Westport location. Enter through private gates into a tranquil sanctuary, where meadow views & the soft outline of the home's romantic arched windows set a tone of understated elegance. The warm and inviting interiors offer flexibility & ideal flow, with a formal

  Julie Vanderblue Higgins Group Real Estate

  61 Clapboard Hill Rd, Westport, CT 06880
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  /40

  $3,950,000

  • 5 Beds
  • 7 Baths
  • 5,771 Sq Ft

  116 Roseville Rd, Westport, CT 06880

  Tucked away on a picturesque property with a peaceful pond and complete privacy, this custom-built home is truly exceptional. From the moment you step onto the welcoming front porch, you'll feel the warmth and quality throughout. The sunlit kitchen is beautifully appointed with top-of-the-line appliances and a built-in banquette by the cozy fireplace, opening seamlessly to the inviting family

  Julie Vanderblue Higgins Group Real Estate

  116 Roseville Rd, Westport, CT 06880
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  /40

  $3,300,000

  • 5 Beds
  • 4 Baths
  • 2,944 Sq Ft

  3 Nassau Rd, Westport, CT 06880

  Modern coastal living on a quiet cul-de-sac in Westport's Saugatuck Shores. Completed in 2021, this five-bedroom, four-bath home spans more than 3,700 sq ft of finished space with a thoughtful open layout and timeless design. The main level features 9-ft ceilings, a sunlit living room with gas fireplace, and large windows framing serene water views. The kitchen offers custom cabinetry, quartz

  Judy Michaelis Coldwell Banker Realty

  3 Nassau Rd, Westport, CT 06880
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  /7

  $4,700,000

  • 6 Beds
  • 5.5 Baths
  • 6,000 Sq Ft

  11 Wake Robin Rd, Westport, CT 06880

  Welcome to 11 Wake Robin Road Located in the sought-after Greens Farms area of Westport, this dramatic new construction sits on a quiet, desirable cul-de-sac. This 6,000+ sq ft contemporary colonial spans three finished levels with 9-foot ceilings throughout and will feature 6 bedrooms and 5.5 bathrooms. Meticulous craftsmanship, elegant finishes, and abundant natural light combine to create a

  Judi Lake The Riverside Realty Group

  11 Wake Robin Rd, Westport, CT 06880
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  /40

  $3,750,000

  • 7 Beds
  • 9 Baths
  • 10,104 Sq Ft

  249 Greens Farms Rd, Westport, CT 06880

  Storied and superbly restored, 'The Lookout' at 249 Greens Farms Rd blends the grandeur of a 1907 Victorian with todays modern luxury. Privately set among perennial gardens and antique copper beeches, this iconic 16-room residence offers a gracious floor plan with elegant formal spaces, a chefs eat-in kitchen, media room, wine cellar, and inviting family areas. Original architectural details

  Kim Harizman Compass Connecticut, LLC

  249 Greens Farms Rd, Westport, CT 06880
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  /31

  $4,495,000

  • 3 Beds
  • 3.5 Baths
  • 3,236 Sq Ft

  32 Edgewater Hillside, Westport, CT 06880

  A Rare Waterfront Masterpiece at Compo Beach: A breathtaking coastal retreat where architecture, craftsmanship, and setting unite in rare harmony. Designed by a celebrated architect and built by one of Westport's most respected builders, this sophisticated beach house captures panoramic water views from every room. Each space is bathed in natural light and oriented toward the ever-changing beauty

  Cyd Hamer William Pitt Sotheby's Int'l

  32 Edgewater Hillside, Westport, CT 06880
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  /35

  $3,295,000

  • 5 Beds
  • 4.5 Baths
  • 3,200 Sq Ft

  26 Treadwell Ave, Westport, CT 06880

  26 Treadwell Avenue is where historic charm meets a modern edgy vibe. Reimagined from the ground up in 2025 by Michael Greenberg, this 1894 Victorian Farmhouse has been transformed into a statement of refined design and craftsmanship. Notable features include exposed beams, white oak floors that ground the space, and curated architectural finishes that make every room feel intentional. Set on a

  Kim Harizman Compass Connecticut, LLC

  26 Treadwell Ave, Westport, CT 06880
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  /40

  $5,500,000

  • 6 Beds
  • 9 Baths
  • 9,601 Sq Ft

  10 Debra Ln, Westport, CT 06880

  Stunning 6 Bedroom 9600SF (including all 4 levels) Colonial in the heart of Westport. Built by Bluewater Home Builders, this stunning custom residence is situated on a private cul-de-sac in the central Hunt Club area. The traditional design boasts exceptional interior details, including soaring ceilings, beamed and coffered accents, shiplap paneling, and sleek millwork throughout all finished

  Linda Skolnick Coldwell Banker Realty

  10 Debra Ln, Westport, CT 06880
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  /6

  $4,395,000

  • 7 Beds
  • 7.5 Baths
  • 8,203 Sq Ft

  20 Morningside Dr S, Westport, CT 06880

  Embrace grandeur in this meticulously crafted four-level estate offering over 8,200 square feet of finished living space. Designed for connection, the main level flows seamlessly between a chef's kitchen with walk-in pantry, open dining and living spaces, and a cozy family room all anchored by three fireplaces that create warmth and atmosphere throughout. Upstairs, the primary suite offers a

  John Schiaroli Coldwell Banker Realty

  20 Morningside Dr S, Westport, CT 06880
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  /30

  $3,100,000

  • 3 Beds
  • 2.5 Baths
  • 4,243 Sq Ft

  118 Roseville Rd, Westport, CT 06880

  A sexy modernist concrete retreat designed by Frank Lloyd Wright protege Francis Barry Byrne, this home is a masterwork of form, function, and sustainability. Thoughtfully built using the Golden Ratio, it sits high on a hill with panoramic views of ancient rhododendrons and oaks. Inside, limestone walls, minimalist lines, and warm natural light create a space that is both bold and serene. The

  Meredith Cohen Serhant Connecticut, LLC

  118 Roseville Rd, Westport, CT 06880
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  /40

  $4,435,000

  • 4 Beds
  • 4 Baths
  • 4,446 Sq Ft

  11 Sterling Dr, Westport, CT 06880

  Nestled in privacy by nearly 100 arborvitaes, this ultimate retreat on a rare double lot is just steps from Old Mill Beach & Compo Beach. The home distinguishes itself by offering water views from nearly every room & from the expansive decks located on multiple levels. Fully remodeled & expanded in 2018, this thoughtfully designed home features oversized windows to enjoy spectacular sunrises &

  Janice McGrath O'Brien William Raveis Real Estate

  11 Sterling Dr, Westport, CT 06880
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  /39

  $3,500,000

  • 5 Beds
  • 6.5 Baths
  • 5,789 Sq Ft

  221 Greens Farms Rd, Westport, CT 06880

  THE BEDFORD HOUSE - Architecturally and historically significant estate in coveted Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's most superb homes. Set on 2.33 acres with a gunite pool/spa, court and a 2400 sq ft barn featuring a 3-car garage, loft & more, the estate blends timeless elegance with modern comfort. Originally built in 1904 and designed by

  Leslie Riback Coldwell Banker Realty

  221 Greens Farms Rd, Westport, CT 06880
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  /40

  $3,550,000

  • 5 Beds
  • 8 Baths
  • 7,359 Sq Ft

  111 Sturges Hwy, Westport, CT 06880

  Welcome to 111 Sturges Highway, the pinnacle of refined elegance and timeless design. A circular drive framed by majestic stone walls sets a distinguished tone upon arrival, while a second driveway provides access from a coveted quiet street. Graceful columns evoke the grandeur of a Southern mansion, while sweeping lawns and specimen plantings create a park-like setting that ensures privacy and

  Julie Vanderblue Higgins Group Real Estate

  111 Sturges Hwy, Westport, CT 06880
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  /14

  $3,395,000

  • 5 Beds
  • 4.5 Baths
  • 5,056 Sq Ft

  16 Burr School Rd, Westport, CT 06880

  A masterful full renovation by acclaimed Coastal Luxury Homes, this extraordinary modern residence redefines sophistication in the heart of Westport. Set on a pristine, private acre on a coveted cul-de-sac, the home dazzles with soaring ceilings, dramatic walls of glass, and exquisite luxury finishes throughout. Designed for the way you live today, it offers two primary suite options, an

  Danna Rogers Higgins Group Bedford Square

  16 Burr School Rd, Westport, CT 06880
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  /38

  $3,899,000

  • 4 Beds
  • 4.5 Baths
  • 4,693 Sq Ft

  11 Edgewater Hillside, Westport, CT 06880

  COMPO BEACH WATER VIEWS at this picture-perfect beach house. Edgewater Hillside is the best-kept secret at Compo Beach, a private Hamptons-style cul de sac where each home is prettier than the next and water views abound. This exceptional residence combines timeless design with high-end amenities and so much space to live and entertain, walking distance to Compo Beach and Old Mill Beach, and

  Cyd Hamer William Pitt Sotheby's Int'l

  11 Edgewater Hillside, Westport, CT 06880
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  /26

  $3,695,000 New Construction

  • 6 Beds
  • 7 Baths
  • 5,497 Sq Ft

  2 Webb Rd, Westport, CT 06880

  Winner of the prestigious 2025 HOBI Award for "Best In Town Spec Home" In CT! A rare opportunity to own a showcase property in one of Connecticut's most desirable neighborhoods, on one of the most popular, quiet cul-de-sacs in Westport! 3 miles to train. Walk to Post Rd shops/restaurants, Winslow Dog Park, Main St, Library, and Levitt Pavilion! New Construction home with Pool. Traditional lay out

  Lori Popkin Coldwell Banker Realty

  2 Webb Rd, Westport, CT 06880
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  /16

  $4,299,000 New Construction

  • 5 Beds
  • 6 Baths
  • 4,879 Sq Ft

  5 Franklin Ave, Westport, CT 06880

  Nestled in one of Westport's most desirable walk-to-town neighborhoods, this exceptional new construction home combines timeless charm with modern luxury. Designed by acclaimed architect Judith Larson and crafted by trusted builder Redcoat Homes, this residence offers the perfect balance of style and functionality. Located on a level third-acre on a quiet cul-de-sac, the property is beautifully

  James Lanzaro Compass Connecticut, LLC

  5 Franklin Ave, Westport, CT 06880
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  /40

  $4,350,000 New Construction

  • 7 Beds
  • 7.5 Baths
  • 6,679 Sq Ft

  102 Compo Rd S, Westport, CT 06880

  THE ESTATES AT COMPO SOUTH - SIR Development presents the last of two luxury residences set back on beautiful property, each with their own distinct Modern style and pool. Officially designated by the State of CT as a Scenic Roadway, this location offers ultimate convenience to every amenity that makes Westport one of the most highly desired towns in the nation. This elevator-ready home begins

  Doug Bross Coldwell Banker Realty

  102 Compo Rd S, Westport, CT 06880
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  /26

  $3,999,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,710 Sq Ft

  13 Terhune Dr, Westport, CT 06880

  Welcome to this beautifully crafted new construction home in the heart of Westport, where timeless design and thoughtful details come together to create a luxurious space. From the moment you step inside, you're welcomed by a bright and open floor plan with high ceilings and wide-plank flooring that runs throughout the main living space. Natural light fills every room, highlighting the custom

  Sara Santos Coldwell Banker Realty

  13 Terhune Dr, Westport, CT 06880
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  /36

  $3,200,000 New Construction

  • 4 Beds
  • 5 Baths
  • 3,800 Sq Ft

  171 & 169 Compo Rd S, Westport, CT 06880

  Stunning 3800+SF of new construction, tucked well away from the road offering a private setting on a .50 acre parcel with UNIQUE potential. Offering fabulous proximity & convenience to Saugatuck train, Longshore town-golf club, Compo Beach and Downtown all via sidewalks. Together, 171 & 169 Compo Rd. S. make up a .50 acre and offer a NEW house, with potential for a pool and separate guest house.

  Tanya Sprague William Raveis Real Estate

  171 & 169 Compo Rd S, Westport, CT 06880
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  /23

  $3,785,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,204 Sq Ft

  3 Laurel Ln, Westport, CT 06880

  Discover the epitome of elegance and sophistication on a quiet street, in a coveted area in Westport! Stunning new luxury construction designed by renowned Coastal Luxury Homes. Known for their architectural brilliance & unparalleled craftsmanship, Coastal Luxury Homes are a testament to innovative design & meticulous attention to detail. The rich architecture features flowing lines, glass

  Julie Vanderblue Higgins Group Real Estate

  3 Laurel Ln, Westport, CT 06880
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  /24

  $925,000

  • 1 Bed
  • 2.5 Baths
  • 2,548 Sq Ft

  185 Regents Park, Westport, CT 06880

  Welcome to 185 Regents Park, an award-winning gated community in Westport offering an exceptional blend of luxury, privacy, and convenience. From the moment you arrive, you'll appreciate the beautifully landscaped grounds and 24-hour security. Step inside this elegant townhouse and be greeted by a grand, light-filled foyer with double skylights that opens to a spacious living and dining area. The

  Kathleen Blackall William Raveis Real Estate

  185 Regents Park, Westport, CT 06880
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  /6

  $7,995,000

  • Land
  • 12.3 Acres
  • $650,000 per Acre

  109 Morningside Dr S, Westport, CT 06880

  109 Morningside Drive South is an exceptional and rare offering in the highly sought- after Greens Farms neighborhood in Westport CT. Spanning 12.3 acres, this expansive property presents a unique opportunity to create a one-of-a-kind estate in one of Fairfield county's most desirable locations. Nestled amongst prestigious homes, this property offers endless potential for those seeking to build

  Jenny Bentley The Riverside Realty Group

  109 Morningside Dr S, Westport, CT 06880
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  /6

  $11,795,000

  • 5 Beds
  • 7 Baths
  • 6,050 Sq Ft

  14 Owenoke Park, Westport, CT 06880

  Bluewater Home Owenoke Opportunity Knocks Again! Another beach masterpiece is underway and this 6050 sqft 5BR/3Car garage designed home with private yard, pool with spa, pond views and walking distance to Compo Beach will be ready Spring 2026. Enjoy this new beach construction living in the heart of Westport while peacefully tucked away on a private cul-de-sac.

  Deirdre Andreoli Compass Connecticut, LLC

  14 Owenoke Park, Westport, CT 06880
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  /24

  $1,699,000

  • 4 Beds
  • 2.5 Baths
  • 3,074 Sq Ft

  42 Kings Hwy S, Westport, CT 06880

  Step into this beautifully renovated modern home, where refined craftsmanship meets contemporary elegance. The grand foyer opens to a stunning living room with soaring double-height ceilings and a dramatic floor-to-ceiling stone fireplace. The gourmet chef's kitchen impresses with custom cabinetry, Viking appliances, quartz countertops, and a spacious eat-in area. Designed for effortless

  Dannel Malloy NestSeekers International

  42 Kings Hwy S, Westport, CT 06880
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  /38

  $1,200,000

  • 2 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  220 Lansdowne, Westport, CT 06880

  Incredible opportunity to own at Lansdowne, one of Westport's most desirable gated communities. This elegant townhouse offers spacious, sun-filled living with beautiful architectural details and serene outdoor views. The large living room features a cathedral ceiling, hardwood floors, and a fireplace, leading to a bright sunroom with sliding doors to an oversized patio overlooking a picturesque

  Patricia Shea Coldwell Banker Realty

  220 Lansdowne, Westport, CT 06880
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  /17

  $1,199,000

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  483 Main St, Westport, CT 06880

  Located just minutes from trendy downtown Westport, this inviting split-level home combines comfort and convenience. Set on over a quarter acre of level, fenced-in property, it offers plenty of space for outdoor enjoyment. Step inside to a bright and welcoming living room featuring an oversized picture window, hardwood floors, and a wood-burning fireplace. The formal dining room opens to a

  Jodi Gutierrez Alliance R.E. Consultants

  483 Main St, Westport, CT 06880
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  /23

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  26 Crescent Park Rd, Westport, CT 06880

  Beautifully maintained single-family home offering 3 bedrooms and 2 full bathrooms, with hardwood floors throughout, perfectly move-in ready, this home provides comfortable living with a thoughtful layout, over 1100 sq ft, a great condo alternative. Located in the heart of Westport, you'll enjoy convenient access to all the town's amenities-shops, restaurants, beaches, and more-while commuters

  Karim Douich William Raveis Real Estate

  26 Crescent Park Rd, Westport, CT 06880
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  /39

  $899,000

  • 4 Beds
  • 3 Baths
  • 3,054 Sq Ft

  23 Bridge St, Westport, CT 06880

  Nestled back on a .31 Acre site is an intriguing circa 1900 converted barn/carriage house. This property is unique in many ways, as it has spacious rooms, smallish rooms, an interesting flow, guest living area in the walkout lower level, charming stone patios, garden areas and an elegant pool. Plus, one can walk to the Saugatuck station in 5-7 minutes! RARE! Because this property started life as

  Karen Curtis William Pitt Sotheby's Int'l

  23 Bridge St, Westport, CT 06880
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  /40

  $9,495,000

  • 6 Beds
  • 11 Baths
  • 11,445 Sq Ft

  5 Hidden Hill Rd, Westport, CT 06880

  Stunning, one-of-one custom home on a private Compo Beach hilltop with sweeping views of Long Island Sound. This Lucien Vita estate was comprehensively refurbished in 2024 to include designer paint treatments, wall coverings, all new lighting and custom window treatments. Luxurious spaces merge impeccable architectural detail and craftsmanship to create distinctive indoor and outdoor living on 4

  Cyd Hamer William Pitt Sotheby's Int'l

  5 Hidden Hill Rd, Westport, CT 06880
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  /40

  $2,850,000

  • 4 Beds
  • 5 Baths
  • 5,207 Sq Ft

  123 Greens Farms Rd, Westport, CT 06880

  Classic Greens Farms Colonial - Timeless Elegance Meets Modern Comfort ~ Nestled in one of Westport's most desirable neighborhoods, this beautifully updated Center Hall Colonial offers the perfect blend of timeless charm and modern luxury. Ideally located just minutes from Sherwood Island State Park-with its miles of golden sand beaches, scenic picnic areas, and sweeping views-this home provides

  Shalini Madaras Silver Pine Real Estate

  123 Greens Farms Rd, Westport, CT 06880
• 

  

  /23

  $599,000

  • 3 Beds
  • 1.5 Baths
  • 920 Sq Ft

  9 Crescent Park Rd, Westport, CT 06880

  Welcome to this charming 3-bedroom, 1.5-bath ranch in the heart of Westport - the perfect blend of comfort, convenience, and low-maintenance living. With a brand-new roof and vinyl siding, this home is ready for years of worry-free enjoyment. The inviting living room features a cozy fireplace, creating a warm and welcoming space to relax or entertain. Thoughtfully designed for one-level living,

  Karim Douich William Raveis Real Estate

  9 Crescent Park Rd, Westport, CT 06880
• 

  

  /17

  $1,450,000

  • 3 Beds
  • 2.5 Baths
  • 1,549 Sq Ft

  113 Kings Hwy N, Westport, CT 06880

  Amazing Opportunity! Charming 1920"s colonial with wonderful 1416 sq ft legal rental cottage. Bright sunny front house freshly painted and beautifully maintained. Hardwood floors throughout, newer kitchen, delightful sun room, perfect for home office. MBR w/charming dressing room and w/i closet plus 2 additional brs and hall bath. Cottage features a great 2 bedroom apartment with vaulted ceiling

  Regina Kendig William Raveis Real Estate

  113 Kings Hwy N, Westport, CT 06880
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  /21

  $1,300,000

  • 3 Beds
  • 2 Baths
  • 1,609 Sq Ft

  56 Partrick Rd, Westport, CT 06880

  Westport * 3BR ranch on 1.67-acre private knoll * Hardwood floors * Newer windows * Underground electric * 0.5 mi to Partrick Preserve. Set on a quiet interior lot surrounded by mature trees, this one-level 3-bedroom, 2-bath home at 56 Partrick Road offers the privacy of a country setting just minutes from Westport's vibrant downtown. Built in 1966, the 1,609 sq ft residence features hardwood

  Kim Burke Berkshire Hathaway NE Prop.

  56 Partrick Rd, Westport, CT 06880
• 

  

  /40

  $1,550,000

  • 4 Beds
  • 4 Baths
  • 2,484 Sq Ft

  5A Sunrise Rd, Westport, CT 06880

  Discover this stylish contemporary home in Westport's highly desired Saugatuck area - just a 7-minute walk to the train station, making it a commuter's dream. Enjoy being steps from Saugatuck Rowing Club, top restaurants, and the town's most vibrant spots. The open-concept main level features recessed lighting, a living room with fireplace, dining area with deck access, and a modern U-shaped

  Louise Petersen Century 21 AllPoints Realty

  5A Sunrise Rd, Westport, CT 06880
• 

  

  /40

  $2,785,000

  • 4 Beds
  • 3.5 Baths
  • 5,434 Sq Ft

  6 Nutcracker Ln, Westport, CT 06880

  A rare Westport retreat blending serenity, sophistication & resort-style living. Privately set at the end of a quiet cul-de-sac off Bayberry Lane, this elegant four-bedroom, three-and-a-half-bath home offers over 4,600 sq ft of sun-filled living space surrounded by beautifully landscaped grounds. The property's two private acres feel like a personal park-complete with mature trees, curated

  Michelle Sperry Coldwell Banker Realty

  6 Nutcracker Ln, Westport, CT 06880

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